


The Spider and The Fly

by cordeliadelayne



Series: An Angel's Contract [2]
Category: Supernatural
Genre: Betrayal, Denial of Feelings, F/M, Kissing, Light Angst, Mild torture, Mildly Dubious Consent, POV Ruby, Sex, but not as sneaky as ruby, castiel is sneaky, ruby plots, trust is a curious thing
Language: English
Status: Completed
Published: 2016-09-28
Updated: 2016-09-28
Packaged: 2018-08-17 09:23:11
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 10,014
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8138915
Author URL: https://archiveofourown.org/users/cordeliadelayne/pseuds/cordeliadelayne
Summary: Castiel thinks he’s using Ruby to get at Lilith. Ruby thinks she’s using Castiel to keep alive. And the Winchesters get caught in the middle.





	

**Author's Note:**

> Sequel to God Is Not Dead, Nor Doth He Sleep. Set roughly between 410 - Heaven and Hell and 411 - Family Remains.
> 
> Originally posted to Livejournal in 2009.

**Present**

Ruby crawled along the ground on her hands and knees, pausing every so often to catch her breath and tenderly make sure that her insides weren’t about to become her outsides. She’d known this was going to be a tough assignment, but knowing and _knowing_ , well, some days she was just as stupid as a Winchester.

Her hair hung about her face and she tried to toss her head back to get the loose strands out of her mouth. The gravel of the parking lot bit into the wounds on her hands and her whole body ached but she had no choice but to keep going like this; she’d tried walking to her motel room but the world had tilted disastrously on its axis after the first attempt and she’d quickly given up. Besides, she knew that making an entrance like this would probably work out to her advantage.

Although it was a dark and cloudy night and out of season, so there were hardly any customers about to see her, it didn’t stop the hairs on the back of her neck from standing up as she got closer to her room. She was being watched.

Lurking in the shadows a little distance away, two angels stood side by side, watching the demon's progress with unblinking eyes.

“Are you going to _comfort_ her?” Uriel asked, breaking the silence with the most unangelic sneer in his voice Castiel had ever heard. How Anna had had the temerity to suggest that angels were totally emotionless, he would never know. Just because they acted out of obedience did not make them any less than the humans use of instinct. It certainly wasn’t something he could ask her, or discuss with his fellow angels; questions like that were far too dangerous to give voice to.

“It is expected,” Castiel said, his head lowering slightly. He could sense Uriel’s disapproval no matter where he was, even though orders were orders. Or maybe _because_ orders were orders. The lines were getting blurred and Castiel was only interested in doing as he was told; anything else was unimportant.

“Indeed,” Uriel said and Castiel seemed to think he was replying to his thoughts rather than his words for it took some effort for him to keep his wings from bristling at the imagined censure.

“Her observations will prove useful,” Castiel said instead. A lot was riding on Ruby’s cooperation. Too much, perhaps.

“If she survives the initiation,” Uriel said. His tone clearly indicated that he didn’t believe she would, as did the brief flicker of the thought across Castiel’s mind. Castiel managed not to flinch. Just.

“She has proven surprisingly resilient already.” Castiel tried to keep any hint of emotion out of his voice; it would not do for Uriel to think he cared about what happened to the demon. She was a necessary tool in the fight against Lucifer and that was all.

Uriel huffed a sceptical laugh but said nothing. In a silence that once would have been companionable, but now lay awkwardly about their shoulders, they continued to watch the demon as she struggled to make it to her motel room. If he had been alone Castiel would have gone to her, just as he would any of his Father’s creations who were trying to atone for their sins, but such an action was impossible in his present company. Uriel saw such compassion as a weakness and Castiel’s light was already dimmed in the other angel’s eyes; he was becoming accustomed to picking his battles.

“Such fornication is beneath you.” _Beneath us._

Castiel continued looking straight ahead, his lips pursed. It would not do to allow Uriel’s words to force a reaction out of him. His brother meant well. He only had Castiel’s best interests in mind, after all.

“It is necessary for Ruby to believe she has something with which to blackmail me. And I her.”

Uriel snorted, an undignified sound that seemed to startle him as much as it did Castiel. “As you say.”

Before Castiel could ask him what he meant – before he had even had a chance to decide whether that was an avenue he wished to pursue – Uriel was gone. He had other tasks to complete and they did not include watching over his Brother’s fornication with a demon.

Castiel sighed. There were days very much like these when he wondered what he was doing. But he only allowed himself a moment’s contemplation before he was striding towards Ruby’s motel room, vanishing from sight before he had taken more than a few steps.

Ruby had just managed to stand up, fumble for and retrieve her key from her back pocket, open the door and then close it when Castiel appeared in front of her, causing her to jump back and open her wounds some more.

“Goddamit, Cas!” she yelped.

“Do not blaspheme in front of me, Demon,” Castiel growled.

“Oh, whatever,” Ruby replied, sinking to the floor. “You freak,” she added for good measure.

For once Castiel was utterly speechless, staring at her with such a confused look on his face that Ruby would have laughed if she didn’t think she’d do herself more harm than good.

“Are you gonna fix me or are you gonna smite me? ‘Cause I’m just a shade above caring.” Her heart was hammering in her chest and she daren’t look up at him but she needed to retain some sort of balance after tonight’s debacle, and this was it.

She was gratified when a moment later Castiel kneeled down to where she was sitting and placed his hand on her stomach.

“This is going to hurt,” he said and if she didn’t know better she’d swear he was pleased about that. But she couldn’t really focus on an angel’s emotions when the hand on her stomach was suddenly pressing into her so painfully she thought it might pass right through her and as her vision greyed out the last thing she heard before she lost consciousness were her own desperate screams.

\+ + + + +

When Ruby awoke she rapidly became aware of two very different sensations. One was a warmth that seemed centred on the base of her spine. The other was someone carding their fingers through her hair. They stopped the moment she drifted back to consciousness even though she hadn’t opened her eyes, and continued a second later. The action was surprisingly comforting and she decided to just enjoy the sensations – it wasn’t as if anyone else in her life was going to be as gentle.

And then she realised that she was naked under the covers of this bed and her eyes shot open. Castiel was staring down at her, implacable as ever, but he continued to move his hand through her hair as if it were the most natural action in the world so she let her eyes fall shut.

“Did you succeed in reaching the inner sanctum?” Castiel asked, breaking the silence.

Ruby sighed and opened her eyes. “Not yet.”

Castiel regarded her critically. She shivered but didn’t say anything. “So what did you succeed in doing?” The reproach in his tone was clear. Ruby resolutely did not feel guilty about it. Absolutely not.

“Well…”

**Two Days Ago**

Ruby didn’t have many contacts in the demon underworld anymore, certainly not as many as she liked to let the Winchester’s think she did. Joining with the brothers, no matter her reasons, was regarded with suspicion by those high up enough to know that there was a war on. But the old style demons, those that had forgotten all about their own humanity? A lot of them were stupid enough to believe whatever web of lies she spun for them.

Rule 1 of Demonology 101: Demons lie.

She was at a bar in a dingy old mining town, sipping at a beer and eyeing the clientele. They were the usual working-class schmuks eking out a paltry living and then heading to the bar to drink away their earnings and to hook up with the waitresses/working girls. Ruby nodded to a couple of them, trying to give them her best “hey, just a girl looking for a bit of fun, not treading on anyone’s toes” look. She wasn’t sure she was totally successful but no one’s pimp made eyes at her, so she figured she was going to be left alone.

She kept one eye on the exit, noting the quickest ways past the crowds if anything happened. She noted where the bar tender kept his guns (one under the bar, the other in the first aid kit by the bathrooms), whether any cops showed up (none), whether any fights broke out (two, and one of them only got heated enough for a bowl of peanuts to go flying) and anything else that she might need to put to her advantage.

She settled down on her stool and took a sip of her beer. Hopefully she looked like a college girl, maybe dumped by a boyfriend? She practised a few frowns and moping looks in the mirror above the bar. Or maybe a girl cruising for some action? She flicked her hair out and pouted. Then she shrugged. She’d just have to play it by ear.

A couple of rednecks playing pool called her over but she just smiled and shook her head. The beefier guy looked like he was going to come towards her, and Ruby shifted a little in her seat, but his friend kept a hand on his arm and shook his head and they both turned back to their game. But Ruby kept a watchful eye on them all the same. One complication at a time.

Rule 2 of Demonology 101: Demons are only out for themselves. Unless they’re too dumb to know better.

She’d been there about an hour, sipping on the same drink and successfully blending into the crowd, when they entered. They had a swagger that was unmistakable, a “fuck me if you dare” look in their eyes, which marked them out as demons on the lookout for a fuck and a kill, and not necessarily in that order. They went over to the bar and ordered a round of drinks, the older (and uglier), snagging his arm around the waitress and whispering something in her ear that had the young blonde turning a shade of red Ruby had never seen before.

Finally seizing her moment Ruby stood up and downed the rest of her drink in one. Then she pulled her jacket open, pushed up her T-shirt so she was showing off her body’s enviably flat stomach and pulled her hair around her shoulders. The next step was to saunter confidently to the bar, flashing the newcomers a flirtatious grin and leaning in close to talk to the server, pushing her breasts out and tilting her leg back so it just about came off the floor. Easy.

“Let me,” the younger demon said. Ruby cast him a quick sideways glance and then smiled. Too easy.

“Same again,” she said to the barman who nodded and fetched her a beer.

“Stan,” the demon told her.

“Samantha,” Ruby replied. She wondered what Sam would say if he knew she’s purloined his name and tried very hard to keep the smirk off of her face, but there was no way she was going to use her own name just yet. She might be a relatively small fish in a big pond, but she’d gone against Lilith. That kind of thing got you noticed.

“Beautiful name, for a beautiful lady,” Stan said, leaning forward and kissing her cheek. She rolled her eyes at the barman but decided to play along.

“Thanks,” she said once he’d moved back out of her personal space. She smiled brightly but inwardly she was calculating her next move. Fun as it would be to see these guys cause mayhem, she needed to get them outside where she could question them properly.

“Come here often?” the demon asked, winking at her and then downing his drink in one. Ruby kept the smile plastered to her face and leaned forward. The demon’s eyes never strayed above her chest.

“How about we take this…outside.”

The demon licked his lips and nodded. “Sure.” Ruby bit the inside of her mouth to stop from grinning too much when the demon almost tripped over himself in his rush to get outside. She followed far enough behind to catch the older demon’s eye and he followed her. Never let it be said she didn’t take the obvious route when it presented itself.

As soon as she stepped into the stinking alleyway by the bar she swung around, lifted the knife she’d borrowed back from the Winchesters, and sliced Butt Ugly’s throat. He fell to the floor without a sound. Then she continued to turn back to the younger demon, and used her momentum to push him up against the wall, knife at his throat.

Rule 3 of Demonology 101: Demons can be taken by surprise just as easily as humans.

“You’ve seen what this can do,” Ruby snarled, pressing the knife close to the demon’s meat suit. “Answer a couple of questions, and I’ll let you go.”

The demon leered at her and shook his head. Ruby frowned.

“I don’t know what crap shoot you think you’re aiming for here, but I…”

But whatever Ruby was going to say was silenced by a forceful blow to her head that had her plowing forward into the demon, her knife silencing him forever.

+++++

When Ruby awoke she found herself trussed up like a turkey, her arms chained to a wall above her head and her legs just about reaching the floor, but chained as well. She pulled at them a little but even with demon strength she didn’t think she was going to get out that way. She chanced a look around the room and was heartened for the moment that she was alone.

It seemed like a typical demon’s hideout – cold and dank and smelling of blood and sulphur. She could make out people walking past outside through the only window in the room. A window high up near the ceiling and with bars across it. She figured then she must be in a basement and it had to be in a central part of…well, wherever she’d ended up, for there to be that much foot traffic.

She sighed at the tortuous looking implements laid out on the table near the back wall and the dentist’s chair in the middle of the room. That at least was the same old, same old.

It was hard to tell if she was badly hurt, but she didn’t think there was anything wrong with her, save the bump she felt sure was forming on the back of her head.

Rule 4 of Demonology 101: Demons heal. Fast.

After what must have been an hour Ruby heard the door click open and a figure stood in the doorway. She could make it out as male, but that was about it, until he took a couple of steps into the room, as if called by her curiosity. Ruby eagerly soaked in the man’s appearance. He was gorgeous, all hard lines and soft curves in just the right places, his tight jeans accentuating what Ruby could just make out as the most perfect ass she’d ever seen. He had dark hair and startlingly blue eyes that she wouldn’t mind staring at a little closer.

Rule 5 of Demonology 102: Any demon worth their salt picks out the prettiest host they can find.

“So sugar, got a name?” Ruby asked, her bravado only half faked.

The man smiled, revealing a perfect set of white teeth.

“I do, but I don’t think you’d be able to pronounce it, little girl. You can call me Nate.” And as he spoke a bright light seemed to infuse the room and Ruby could easily make out Nate’s wings reflected on the wall behind him.

And her day took a decided turn for the worse.

**Present**

“And so you were captured by a demon?” Castiel asked her as Ruby took a break from her tale. He was rubbing gentle circles on her bare shoulders and she’d actually started believing he was totally unconscious of the fact that he was doing it. But then again she’d had plenty of opportunities to learn that angels were a whole lot wackier than demons, so maybe he knew exactly what effect he was having on her goosebumped flesh.

“That’s right,” Ruby said. “Didn’t tell me his name but I figure he’s pretty high up the food chain.” She slanted her eyes over to Castiel’s face and then back again. Nope. Still too hard to tell what the angel was thinking.

Castiel nodded, deep in thought.

“And it was he who caused your injuries?” he asked after a moment of silence, where each of them had been running through various scenarios in their heads.

“That’s right,” Ruby repeated. She hummed slightly as Castiel planted an abstracted kiss against her forehead.

“And now you are closer to Lilith?”

Ruby closed her eyes. “That’s the idea,” she said.

**One Day Ago**

Ruby was still tied to the wall. Still tired. Still cold. Still frightened.

The angel had only shown his wings and then disappeared, in that disarming way she was beginning to associate with the winged freaks. And no one else had appeared to break the monotony.

She was trying to work out what the angle here was. Surely the other angels would know that she was working with Castiel…but no, she seemed to remember them not knowing what was going on was part of the deal. Crap.

So unless her spunky personal angel came to get her she was screwed. And she guessed that wasn’t part of his duties. Only Dean Winchester got that kind of special treatment. She shook her head. Some days she could taste her hate for him.

She turned her head as she heard something in the far corner of the room. It was a quiet banging sound followed by a gurgling.

“I thought you’d appreciate it if I turned the heating on.”

Ruby flinched as the angel, Nate, appeared right in front of her.

“What do you want?” she asked belligerently and tilted her head defiantly. Just because she was tied up in a room with her kind’s mortal enemy, with no way out and no white knight coming to her rescue, didn’t mean she was going to let her guard down.

Rule 5 of Demonology 101: Demons come in two categories – those that are too stupid to be afraid, and those that fake it well.

The angel merely smiled, his eyes crinkling at the corners in a way that Ruby definitely did not find attractive. Much.

She tried to keep eye contact with him, but his unblinking stare was starting to freak her out. Not to mention his blue eyes were reminding her rather forcefully of a certain other angel in her life.

Nate moved forward slowly. There was a certain economy of movements in his gait that she was coming to associate with the angels (and how terrifying was it that she was spending enough time around them to notice?), but also a looseness in his limbs that seemed to indicate he was perfectly comfortable in his current form. Before she had a chance to puzzle out what that might mean for her, Nate had leaned forward and appeared to be smelling her hair.

“What are you…?” Ruby started to ask.

“You smell like angel,” he muttered. His brown furrowed in confusion. Ruby tried to laugh but it come out as little more than a squeak.

“An angel? Why would I…”

Ruby was silenced by Nate kissing her, forcing her lips to part with his tongue and plundering her mouth. She had no time to respond as Nate pulled back almost as quickly as he’d taken what he'd wanted. Ruby licked her lips cautiously, wondering what was going to happen next. To say he was keeping her on her toes was a major understatement.

“You taste like Castiel”.

Ruby’s eyes opened wide, her total surprise undoing any subterfuge she might have tried to display.

“So you do know my Brother then,” Nate murmured. He took in a quick sweeping glance of her body. “You aren’t what I’d imagine his type would be. But then perhaps he’s in his experimental stage.” He chuckled. “Or rebellious. I wonder what Father thinks of one of his precious favourites rutting with a demon?”

“Castiel’s one of God’s favourites?”

“He was Chosen to pull Dean Winchester out of Hell. That’s a pretty juicy assignment for a lowly worker bee.”

Ruby nodded slightly to herself. In a way that made sense. Unless Castiel was seen as expendable. But either way, surely God wasn’t supposed to have favourites?

Rule 6 of Demonology 101: Demons will never understand angels. (Nor would they want to).

“And you know Dean Winchester.”

Ruby shrugged nonchalantly. “I hear things.”

Nate leaned forward again, his lips inches from her mouth. Clearly personal space was an alien concept to all angelic beings. “I think you more than just know things, little girl. I think you make things happen. I thought you were just some two-bit whore out for a little fun, but now I see you’re much more than that. You _know_ things.” He tilted his head. “Tell me your name or I’ll pull out all the bones in your body, grind them up, and feed them back to you.”

Ruby bit her bottom lip. She needed to bluff her way out of this. She needed to think.

But Nate’s eyes were boring into her very essence and his distractedly male body was pressing up against her. She could hear the rustling of his wings even though she couldn’t see them, not even their shadows, and his threatening words danced across her skin, raising the flesh. There was no doubt in her mind that he would, and could, do exactly as he said he would, nor that it would hurt just as much as the torture she had endured in Hell.

“Tell me your name,” the angel repeated, his voice a low rumble of thunder that threatened to deafen her.

“Ruby,” she said quickly, cursing her own weakness as she did so. Other demons cutting into her she had no problem with, but there was something so all-encompassingly terrifying about how utterly alien the angels were, that had her more frightened than she dare ever admit, even when she was fucking one of them. “My name’s Ruby.”

**Present**

“He must have been very inventive,” Castiel said, breaking into her story. “There were some extremely intricate sigils carved into your flesh. Ancient symbols I haven’t seen in centuries.”

Ruby winced at the memory. “Let’s just say he could give Alistair a run for his money.” She paused, and then decided to name the elephant in the room. “Or Dean”.

“Dean did what he had to,” Castiel growled. “I would have thought a demon, of all creatures, would understand that.”

Rudy raised her hands above her head and grabbed the headboard, stretching her whole body right down to the tips of her toes, which she hooked into the covers of the bed and started to pull down slightly, exposing her breasts to the cool air of the room. She was extremely pleased to see that Castiel’s gaze fell from her face to her body; he might be an angel but his vessels muscle memory was definitely male.

“Oh, I understand doing what you have to do, perfectly,” she said. She shifted her legs so they were spread open further, one of them knocking at Castiel’s legs, though he was still laying atop the covers. “I seem to remember a certain angelic being also having to do what they had to.”

Just thinking about the way Nate had kissed her, how his body had pressed into her, never mind the way he’d teased her with fingers and steel had been turning her on. And now she was feeling like herself again she really wanted this angel to hold up his side of the bargain.

Castiel glared at her with an expression usually reserved by parents for their children. Ruby decided it was best not to examine too closely why that thought had her swallowing back a moan.

“Is that all you ever think about?”

Ruby grinned. “Pretty much.” She started pulling at the covers of the bed again, forcing Castiel to stand up and get out of her way as she finally scrunched them up at the end of the bed. “Well, are you getting with the programme or not?” Her eyes focused on his crotch. “’Cause your lower half seems to have started without you.”

Castiel looked down and seemed surprised that he was sporting an erection. “I usually have better control over my vessel,” Castiel murmured. He almost seemed embarrassed, which Ruby found terribly cute, if a little disconcerting. She had no wish to be vaporised by an angel that couldn’t keep his Grace in check.

“Oh, for fuck’s sake,” she muttered as it became clear that Castiel wasn’t about to make the first move.

She reached up and grabbed his tie, pulling him forward. His eyes widened and his arms flailed a moment before angelic refinement returned to him and he carefully placed his arms by Ruby’s sides, his fingers delicately brushing against her hips.

Ruby took advantage of her position to pull Castiel even closer to her, until she was pushing her tongue into his mouth, and he was letting her. She made an animalistic sound deep in the back of her throat as Castiel moved to lie on top of her, his suit and tie rubbing against her sensitive flesh.

Rule 7 of Demonology 101: Demons like sex. A lot.

“Take off your clothes,” Ruby panted, her fingers tangling in Castiel’s tie.

“I don’t take orders from demons,” Castiel retorted.

“That would be a little more convincing if your Johnson wasn’t standing to attention,” Ruby responded. She smiled lasciviously as Castiel strained not to roll his eyes. For a heartless son of a bitch he could certainly be expressive.

“Shut up,” he murmured. But there was no heat to his words as he pulled off his tie and started to undo the buttons on his shirt. Ruby started to help by pulling at the belt of his trousers, her fingers ever so not accidentally at all touching his cock at every opportunity.

Castiel threw off his shirt and Ruby took a moment to admire the way his vessels taut muscles rippled. He was pretty buff for a holy tax accountant, and she could hardly believe that no one but her got to see him like this. Unless of course the angel’s had regular orgies when they weren’t being dicks, which was definitely something she’d like to see.

Castiel moaned as she pressed up against him and began pulling off his trousers. His shoes already lay discarded on the floor.

He closed his eyes and Ruby allowed herself to take moment to just soak up his dishevelled appearance. After all, she might not get another shot at him after this.

He was certainly more emotional than he had been before (unless he was better at faking it than she realised). And though she’d be perfectly happy to take the credit for it, she figured being stuck around humans, especially when they come as attractively packaged as the Winchesters (well, Sam at least, she amended), was the real cause. If being in Hell made most demons forget their humanity, being on earth must be the same way for angels. Maybe it wasn’t surprising after all, that angels could Fall and fornicate and lie and cheat just like the rest of their Father’s children.

“He was very handsome, you know,” Ruby said. “The demon. Put his hands all over me.”

Castiel looked down at her and his lips twitched. “Are you trying to make me jealous?”

“Depends,” she said. “Is it working?”

Castiel opened his mouth to chastise her but he found himself groaning instead as Ruby’s tongue flicked out across the head of his cock. Then she moved her mouth over it and nearly choked as Castiel bucked into her mouth in surprise. But this was hardly Ruby’s first time so she relaxed her throat and let him push his cock into her mouth, her hands coming up to tug gently at his balls.

She stared up at him as she lay there, wondering what he was thinking about. She hoped it was about her and the way she was making him experience emotions whether he liked it or not. But honestly he could be reciting a celestial shopping list to himself for all she knew.

After a few moments she pushed him back, gratified to see the look of disappointment on his face, fleeting though it was. For fun though this was, she had some place else she’d rather the angel had his cock.

“We’re not going to get disturbed, are we?” she asked.

Castiel shook his head. “I have protected us from prying eyes.”

Ruby smiled. “Great. Then in that case, I’m going to need you to fuck me.”

Castiel’s pupils dilated and Ruby surged up and started kissing him, making sure that he could taste himself on her tongue. He pulled her closer, his hands fanning out against her spine.

She could hear herself moaning as he deepened the kiss, putting all his energy into it, until she was so distracted she didn’t notice that he’d aligned himself with her body until he was pushing inside of her.

“Oh, that…that’s it,” she muttered, lost in the feel of him. Her hands snaked around him to his ass, urging him to go deeper.

And so he did. He thrust in to her and then pulled out, a very human smirk on his face as Ruby’s nails dug into his back, urging him on. He surged forward, kissing and biting at her neck as she tilted it up off the pillow, her toes flexing against the bed as she pushed herself up to meet each of the angel’s deep thrusts. Their first coupling had been perfunctory, just one more order he had to follow; this time was more like the desperate rutting of someone who had something to prove. Though what that could be Ruby couldn’t imagine.

Nor did she care right now as Castiel slammed inside of her again and again, until her orgasm was shooting through her, waves of it pulsing through her body until she closed her eyes and gasped as her body spasmed around Castiel’s cock and she felt his body stutter and then seize up as he too came with a guttural cry that made her stomach flip.

She sighed pleasantly as the angel sagged to one side of her, his breathing as harried as her own. The same angel that had thought to protect the motel from demonic and angelic interference, but who hadn’t deemed protecting against human curiosity worth the effort.

The same angel that didn’t realise they were being watched.

“You still haven’t told me how you managed to escape,” Castiel said into Ruby’s hair, leaning forward a little to nibble on her ear.

“Oh, haven’t I?” Ruby squeaked, as Castiel’s fingers dipped inside her. “Not much to tell.”

“I’d like to hear it, all the same,” he replied. He brought his fingers up to Ruby’s mouth and rubbed them over her lips. She darted out her tongue and licked his fingers clean, all the time acutely aware of the angel’s naked body pressed right up against her side. It was exhausting, working for the good guys.

“Okay, well, it’s like this,” she began, staring up at the ceiling so she wouldn’t get distracted.

**One Day Ago**

“Ruby. Ruby. Ru-by.” Each time Nate said her name it was as if he were testing it out on his tongue, changing the tone and modulation to see which one made her wince. Ruby, meanwhile, was concentrating on fighting her rising panic.

“So what do you want, then?” she demanded, a little breathlessly.

He raised his hand and the table she’d spotted earlier with the torture devices on it rolled its way across the room and came to a stop by the angel’s right.

“Answers.”

He picked up a sturdy looking knife with serrated edges and passed it between his hands, judging the weight.

“You could just ask nicely,” Ruby responded, her eyes never moving away from the route the knife was travelling.

Nate chuckled and the hairs on the back of Ruby’s neck stood up.

“All right. Let’s try that. You’re helping the Winchesters?”

Ruby hesitated a moment and Nate smacked her across the mouth with the back of his hand.

“Answer the question.”

“Yes,” Ruby replied. There was no point lying about it – her connection to the Winchesters was well known within certain circles, particularly the ones that Lilith most frequented.

“Are you fucking Castiel?” Nate asked and Ruby nodded. “Why?”

“He’s cute,” Ruby shrugged. Her insolence was rewarded with another backhand across the face; this time the angel drew blood.

“His vessel has certainly been well chosen,” Nate agreed pleasantly, ignoring her blood on his knuckles. “Castiel has always had an eye for the aesthetic.” He took the knife into his right hand and pressed it up against her cheek. “But he wouldn’t fuck a demon just because she battered her eyelashes at him. He is a loyal soldier.” His words dripped with sarcasm. “So he must be following orders. Which doesn’t explain you.”

Ruby stared defiantly back at him. “I can’t help who your Brother gets a hard on for. I’m not gonna turn down a hot fuck.”

Nate’s eyes twinkled and Ruby gulped. Faster than her eyes could see Nate made the sign of the Cross over her body with the knife, slicing at her T-shirt and flesh and making her cry out in pain.

“Yes…lying, cheating, slut. That’s what they call you in the Pit. And out of it.” He leaned forward and pulled at the scraps of her T-shirt and pushed her bra out of the way. His eyes flicked to her face and then he put his mouth over her left nipple and bit down hard enough to draw blood. Ruby cried out but her body surged forward as far as the chains would allow her, waiting for his next touch.

He drew back with a repulsed sneer. “Demons are so easy,” he sighed. “It’s hardly any fun anymore.”

Rule 8 of Demonology 101: Demons think there is a very fine line between torture for punishment and torture for pleasure. (They’re not the only ones. See Rule 3 of Humanity 101).

Ruby tried to answer but he was kissing her then, fierce and hard and all she could do was give in to him. She shivered as he fondled her breasts and then his hands went lower, grabbing at the belt on her jeans and pushing them down her thighs a little. She was already wet and Nate’s fingers didn’t receive any resistance as he began to roughly flick them across her clitoris. It wasn't exactly a pleasant sensation, but then Ruby wasn’t exactly all flowers and light herself.

When he suddenly pulled away and Ruby tried to follow she knew she was lost. Every fibre of her borrowed body was vibrating with need; she’d never felt so turned on in her life.

“Castiel thinks he’s using you. Correct?” Ruby nodded. “To get at Lilith?”

Ruby nodded again and then started to frown. “Can’t you just ring him up for a chat yourself?”

Nate pushed his body up against her, his hard cock pressing into her thigh.

“You know that every family has a black sheep?” he asked. “Well, I’m it.”

Accompanied by a fluttering of wings he twisted her around till she was facing the wall. She could hear him fiddling with his own jeans and then he was pushing her butt cheeks apart and thrusting into her. She screamed at the harsh pain – she and this body hadn’t tried that out before.

“You will go back to Castiel,” Nate told her, punctuating each word with a painful thrust. “And you will tell him you were captured by a demon.” His hand came around her body and his fingers started exploring her clitoris. “And you will tell him that this demon can get you close to Lilith.” He started speeding up both his thrusts and his fingers until Ruby could hardly stand it, her head falling back onto his shoulder, her voice quietly begging for more. But he ignored her, intent only on passing on his message. “And the day after tomorrow you will tell him that I have the sister to the demon destroying knife.” Ruby’s eyes opened wide at that, but the angel plowed on. “And you will convince Castiel and the Winchesters to come to a location of my choosing.”

“And if I don’t?” Ruby gasped, wanting him to punish her for speaking out even as she could feel her orgasm approaching.

“Then I will personally hand you over to Lilith,” Nate said. “And we both know you wouldn’t like that.”

“What if Castiel doesn’t…what if he doesn’t believe me?” she asked. She started rocking on Nate’s fingers, chasing that elusive feeling of completion.

“Don’t worry,” Nate purred, “when I’m done with you, Castiel won't have any trouble believing your story.” And with a flick of his wrist Ruby was coming so hard her vision whited out.

And then she started to scream.

**Present**

“So it all went according to plan?”

“Doesn’t it always?” Ruby asked. She sat up quickly and started hunting for her clothes. “It’s getting late,” she continued before Castiel could ask her what she was doing. “And I didn’t exactly pay for this room.”

Castiel sighed and with a flick of his wrist was dressed in his usual shirt, tie and trenchcoat combo.

“Remind me to take you shopping next time we hit a big city,” Ruby murmured.

Castiel ignored her. “When are you next meeting with the demon?”

“Don’t know. Next day or two, maybe. He didn’t get into specifics.”

Castiel nodded. “Let me know when he does. Same signal as before.

“Right,” Ruby replied. “Very 007.” She headed to the door and paused to look back at him. “You’d make a pretty good James Bond.” She smiled. “Guess that makes me Miss Moneypenny.” She slipped out of the door before he had a chance to ask her what she meant.

“The stench of her sweat on your flesh is revolting”.

“Uriel,” Castiel responded neutrally. He turned around to see his Brother standing stiffly in the corner of the room, making very sure that his vessel’s limbs did not come in to contact with the walls.

“Do you believe her?”

Castiel shook his head. “No. But it only matters that she thinks I do.”

“You’re playing a dangerous game, Brother.” The ghost of concern Castiel could feel in them tempered Uriel’s sharp words. In his own inimitable way Uriel was trying to look out for him.

“I’m just following orders,” he said.

Uriel stared at him, drinking in his dishevelled appearance and the dirtied bed. “Just see that is all you are doing.”

And then he disappeared, leaving Castiel alone with his thoughts.

**The Present – Five Miles From Ruby’s Motel**

Sam Winchester yawned and opened his eyes. He stretched his long limbs, cursing silently at the length of the bed and then glanced over at his brother’s bed. He blinked. And then blinked again.

“Must make a change,” Dean said as he burst through the door, slamming it behind him. “Waking up and finding an empty bed next to you.”

Sam sat up quickly, retort on the tip of his tongue, when he took in Dean’s stance and paused. Dean looked like he hadn’t slept and he was furiously pacing up and down. The expression on his face was one that Sam recognised all too easily – like the bottom had dropped out of his world.

“Dean?” he asked. “Dean – what’s happened?”

Dean laughed mirthlessly and turned to face his brother. “What would you say if I told you your girlfriend was cheating on you?”

“I don’t have a girlfriend,” Sam quickly replied, not appreciating the way this conversation was going.

Dean sighed. “Whatever”. He took a deep breath and launched into an explanation. “I went for a drive last night, came across Ruby.”

“And?”

“She was banging an angel.”

“An angel?” Sam repeated, thoroughly confused. “What angel?”

“Castiel.”

Sam started to laugh but Dean’s expression stopped him cold. “Shit. You're serious.”

Dean nodded and sank down on the edge of his bed. Sam watched him worriedly.

“Are you sure?” Sam asked after a moment. It was hard enough some days to get over the pain of angel’s being nothing like the divine beings he had hoped they were, but he had thought Castiel was on their side. That if not their friend he was at least an ally they could rely on. But fucking Ruby? That was a development that just didn’t compute. Did it mean he had Fallen? Had he ever been on their side? His head started to swim and only Dean’s words brought him back to the moment.

“Oh, yeah, I’m sure,” Dean replied with an exaggerated shudder. “I’ve seen less disturbing visions in Hell.” He lay back on the bed and stared up at the cracked ceiling. This motel was just like hundreds of other’s they’d stayed in; simple and just about clean, with the odd patches of darkness covered up. Not unlike the pair of them, he supposed.

“There has to be an explanation.”

“Yeah? Like what?” Dean snapped. “Cas got a little horny and out of all the millions of humans on the planet he settled on Miss Demon Slut 2008?”

Sam shrugged. His mind was still reeling – it was far too early in the morning to be dealing with this. “So what do we do?” He looked over at his brother and frowned; Dean looked utterly defeated. But then in the blink of an eye he was sitting up, eyes alert, back straight.

“Right now?” Dean asked. “Right now, we go get breakfast. I’m starving.”

**Later That Day**

Sam was sipping at his third coffee when he spotted her. His hands formed fists automatically and nearly broke the handle from his mug. He knew he shouldn’t trust her. He _didn’t_ trust her. Not the way he trusted Dean or Bobby, but her apparent betrayal still itched under his skin.

She came hurriedly into the diner and sat in the booth opposite him, eyes finding the exits and then him.

“Hey, Sam.”

“Ruby.”

He wanted to say more. He wanted to question her. Or throttle her, dragging her essence out of her stolen body. But they were interrupted by the waitress and Sam struggled to keep his feelings in check.

“Coffee. Black,” Ruby told the waitress before she had time to ask. “I need to talk to you,” she told Sam as the waitress retreated to the kitchen with a roll of her eyes at Ruby’s rudeness.

Sam looked up as Dean approached from the bathroom, ignoring Ruby for the moment. Dean did a double-take when he spotted his brother’s companion and they had a hurried conversation with their eyes alone. Sam nodded; for now he’d follow his brother’s lead.

“What do you want?” Dean asked her. If his face was unusually lacking in emotion, Ruby didn’t seem to notice.

“I know where Lilith is,” she announced, treating it with the same reverence she would a discussion of the weather. “And I know how you can capture her.”

Dean looked over at Sam, who half-shrugged; he had no idea what Ruby was playing at either, but he couldn’t deny that he was intrigued.

“And why the hell should we believe you?” Dean asked

Ruby sighed. “Because I happen to be telling the truth.” Dean snorted. “And because the angels say so too.”

“The angels?” Sam repeated.

“Uh huh,” Ruby said. The waitress brought over her coffee and she took a quick sip. Dean and Sam watched her, confusion etched on their faces. Ruby looked like she was lying. And whatever Ruby did, no matter how many lies she touted out, and how often their default setting around her was to accept she was lying and try to work out what about – now she actually looked like she didn’t want them to believe what she was saying in the first place. Which made even less sense than usual. Why would she _want_ them to be on their guard?

But they didn’t have the time to work out why a demon was doing what came naturally. It was time to put their own contingency plan in place. Even if it did mean walking straight into a trap.

“You and the angels best buds now, huh?” Dean asked, finally sitting down.

Ruby shrugged. “Sure.” She pushed her drink away and looked out at the parking lot. “We don’t have time to hang around here. We need to get moving.”

“Moving where?” Sam asked. He followed her gaze but he couldn’t see anything out of the ordinary outside.

“There’s an abandoned warehouse in the next town over. Lilith’s been using it as a meeting place.”

“And why don’t the angels just blow the place up?” Dean asked.

Ruby kept her eyes on the parking lot, not even bothering to glance at the brothers. “They can’t. It’s protected from them.” She paused and Dean thought he detected a slight nervous twitch in her fingers. “Only those with demon blood can enter.”

“Oh, hell no,” Dean exploded at once. He slammed his fist down on the table. Ruby flinched and several diners looked their way.

“Okay,” Sam said into the tense silence that had followed Dean’s outburst.

Ruby nodded, but didn’t look at him.

“No,” Dean said to his brother. “This is bullshit. You are not going in there to face off with Lilith. Not without me.”

Sam sighed and Dean’s veins turned to ice. He knew what that look on his brother’s face meant.

“I have to, Dean. This may be our only chance to stop her.”

“Sam…”

“I don’t need your permission.”

Dean and Sam sat staring at each other, a silent battle amidst the sounds of diners talking and knives and forks scraping against plates.

“It’s decided then,” Ruby said.

No one answered.

“So this is it?” Sam asked Ruby. Ruby smiled at his eagerness and ignored the glare Dean gave her. Sam really was just an over enthusiastic puppy dog when it came right down to it. Or maybe a blood thirsty serial killer, judging by the way he was heading, under her tutelage of course.

“This is it.”

Dean stared up at the building in the otherwise vacant lot. Most of the windows were broken, weeds were growing everywhere and there was a stench about the place that Dean quickly decided didn’t merit investigating further. It didn’t seen like the most obvious hideout for Hell’s Bitch.

“So, what’s the plan, Toto?” Dean asked Ruby. He leaned against the Impala nonchalantly but all his senses were on the alert. He _knew_ this was a trap. Sam knew it was a trap. And yet here they were, walking straight into the Lion’s Den.

Ruby started emptying the rucksack she’d brought with her. “We’ll need the angel’s help,” she told them. “So first thing we do is summon them.”

Even Sam looked confused at that. “Why _are_ you suddenly okay with the angels?” he asked.

“I’m just thinking of you, Sam,” she said. “Lilith’s pretty strong. Best be prepared. It won’t take a minute to…”

Dean and Sam exchanged significant looks as the familiar sound of wings was followed by Castiel’s presence. Ruby stood up quickly, her spell apparently forgotten.

She took a step backwards as Castiel levelled a thunderous look in her direction.

“The weapon is not here.”

“Weapon?” Dean asked. “I’ve heard Lilith called a lot of things, but that’s not been one of them.”

Now it was Castiel’s turn to appear confused. “Lilith? You think Lilith is here?”

Dean looked at Sam and then all three of them looked at Ruby.

“Um, okay, I can explain,” she said, trying to back away as quickly as possible.

Castiel took a menacing step towards her, a faint glimmer of his Grace visible behind his eyes. He had no time to act however, as all four of them suddenly found themselves transported into the middle of the warehouse.

“…the hell?” Dean exclaimed, looking wildly around. “Cas, was that you?”

“No,” Castiel replied. His eyes darted around and it was clear to the others that whatever had brought them there, it was no friend of the angel’s.

Ruby tried to slip away but she cried out when she attempted to step over the circle drawn in chalk on the ground.

“Devil’s Trap?” Dean asked no one in particular as he examined the drawing.

“No,” said Castiel. “Something far more ancient than that.” He whispered a word that none of the others could understand.

“I go by Nate, these days.”

Dean and Sam turned to look where the voice was coming from. The man stepped into the light and smiled at the Winchesters.

“My, my, Dean and Sam. Sam and Dean. Such magnificent specimens. I can see why you spend so much time with them, Castiel. You’ve always appreciated the beautiful.”

“Friend of yours?” Dean asked Castiel with a sneer.

“No.” Castiel paused as Nate stepped in front of him, only the small space created by the chalk line keeping them from touching. “I was told you were dead.”

Nate laughed. “Word of advice, Brother. Don’t believe everything the Old Man tells you.” And he glanced up towards the ceiling.

“Brother?” Sam repeated. “He’s an _angel?_ ”

“In a manner of speaking,” Castiel replied.

“Oh, you wound me,” Nate grinned, putting his hands on his chest. “All our history, everything we’ve done together, and that’s how you repay me?” He turned to address Sam and Dean. “I’m just very good at staying off of Heaven’s radar.” He started walking around the group and they all turned to watch him, careful so that they never had their backs to him. “And of course Ruby was most instructive.”

They all turned as one to look at Ruby, who just shrugged. “I’m a demon, what did you expect?”

Rule 9 of Demonology 101: Demons are pragmatists.

“We had an agreement,” Castiel said.

“Dude!” Dean exclaimed. “You made a deal with a demon? What the hell have you been smoking?”

Castiel looked at Dean in frustration. “I told you once that everyone in this War would have sacrifices to make.”

Dean nodded. “So that’s why you’ve been banging Ruby? Orders?”

Castiel and Ruby looked equally startled. “How did you…?” Ruby started to ask.

“Much as I hate to interrupt this lover’s quarrel,” Nate said, earning him a glare from everyone, “but I believe that we have more important matters to discuss.”

“What do you want?” Sam asked. He stepped as close to the chalk line as he could. Dean reached out to pull him back, before gritting his teeth and letting his arm fall uselessly to his side.

“Sam Winchester. The Boy with the Demon Blood. So much darkness inside of you. I can almost taste it.”

“I’m not afraid of you,” Sam said, his face twisting in disgust.

“No, you’re not,” Nate agreed. He leaned in very close to Sam and both Dean and Castiel braced themselves to intervene. “And that will be Heaven’s downfall.” He smiled as Sam flared his nostrils. “I was just going to turn you over to Lilith, and reap my reward at Lucifer’s side, but maybe I should take you under my wings myself, instead. I could show you what you can _really_ do with those powers of yours and all that wonderful demon blood pumping through your veins. We would be magnificent together.”

Nate raised his hand and ghosted his fingers against Sam’s cheek. Meanwhile Ruby, who had been slowly edging her way around the Trap, slid into Castiel’s personal space. Dean, who was keeping a watchful eye on Sam and Nate saw her pressing something into Castiel’s hands out of the corner of his eye, but he couldn’t quite make out what it was. He looked at her quizzically and was more than a little surprised when she gave him a quick, genuine smile in return and then slid down, as if tying her shoelaces.

Rule 10 of Demonology 101: Demons are like humans. Unpredictable.

Dean turned to look at Castiel who signalled for him to go to the middle of the circle. Frowning, but trusting that the angel knew what he was doing, Dean did so, pulling his brother back with him as he went.

“Dean!” Sam exclaimed, pulling his arm free. “What are you….”

“We didn’t come here to get into a pissing contest with an angel,” Dean hissed.

“No, we came to get Lilith. Only she’s not here and we’re stuck with your angel.”

“My angel?” Dean repeated, incredulously. “We’re only here because of your demon slut…”

“Hey!” Ruby snapped. “How about a little gratitude?”

Dean and Sam turned towards where she was still kneeling, their mouths open, incredulous expressions in perfect synch. They would never, ever, understand demons, and especially not this one.

“Gratitude?” Dean repeated, as if the concept were foreign to him. His eyebrows were practically touching his hairline and his eyes were so wide Ruby would have laughed if she didn’t have other things on her mind.

Nate was watching them all with undisguised amusement and more than a little condescension. “Even in the middle of a war, humans still have an innate capacity to squabble. Most endearing, wouldn’t you say, Brother?” Nate’s eyes flicked towards where Castiel was standing, and his gaze raked over the other angel’s vessel; if the angel within wasn’t such a pain in the ass, Sam wouldn’t be the only one he’d be having some fun with.

Castiel slowly lowered his head in agreement. “Humans are complicated creatures. Full of contradictions.” Castiel held up the object that Ruby had passed to him. It looked like an amulet of some sort, which glittered with an unnatural light. “It’s worth remembering that demons were humans once.”

Nate’s eyes went wide as he scrabbled at the chain around his neck. It was still there, though missing a vital component

“But…how?”

Ruby grinned.

**One Day Ago**

Ruby winced as Nate undid her bonds and she grabbed onto his shoulders to stop herself from tumbling to the ground. Her fingers caught in the chain he was wearing around his neck. As he lowered her none to gently to the ground she saw a glitter of familiar blue liquid.

**Present**

“You should never trust a demon,” Ruby told him. She slipped a knife out of her boot and stood up. “Especially one that used to be a witch.”

**One Day Ago**

“You can follow the design?” Nate asked her, shoving a dusty tome into Ruby’s hands.

“Sure,” she replied, her wounds aching. “But don’t I get something too?” She hopped forward and wrapped her arms around his neck.

“You get me not killing you,” he spat in disgust, pushing her away. “I can’t draw it myself. Get started.”

He turned away and Ruby pocketed his bottled Grace.

**Present**

“Now, that’s more like it,” Dean smiled, nudging his brother in the ribs. Sam just rolled his eyes.

Nate tried to reach out and grab the Grace from Castiel’s hand, but the power of the Trap repelled him.

“Castiel, please,” he begged. “You know what they do to angel’s in the Pit. You know what _He’ll_ do if I have nothing to offer Him.”

Castiel’s face was as blank as usual, though there was a hard glint in his eyes. “You have been working with demons. Killing, torturing, _enjoying_ it." He shook his head. “You are an Abomination. An angel that would dare harm his Brother or Sister, has forfeited his right to his Grace.” Nate cried out in pain as Castiel’s grip tightened on the bottle. “Close your eyes!”

The demon and the humans did just that, closing their eyes and covering them with their arms for good measure too. Even then they could still make out the light they now associated with the death of an angel trying to seep past their eyelids.

After a moment, everything fell dark.

“You can look now,” Castiel told them.

When they did they saw the outline of the angel Nate, outstretched wings and all, imprinted on the furthest wall.

“Cas, are you okay?” Dean asked.

“It had to be done,” Castiel replied. Which wasn’t really an answer to anything, but Dean let it go.

“So, how are we supposed to get out of here?” he asked, looking over at Ruby; she seemed to have all the answers today.

“She who created it; she who destroys it,” Ruby replied. Dean looked blank. “Witch,” she said, taking pity on him. With her knife she sliced into her arm and dripped some of the blood onto the chalk pattern.

Immediately it started to fizzle and spark until the whole pattern was on fire, blueish flames flicking up at the ceiling before dying down completely, with an audible pop.

Ruby smiled proudly. “Easy when you know how.”

“So, what happens now?” Sam asked. His hands were balled into fists, eager for the fight that had been denied him. Dean watched him with saddened eyes.

“I do not know, Sam,” Castiel replied, his mind seeking out answers from above, but receiving no reply. “We need have Faith.”

“Faith?” Sam scoffed. “That’s your answer to everything. Well, I’m not buying.”

He started to stalk off. “Sam!” Dean shouted. “Oh, come on, Sam!” With an apologetic look at Castiel he hurried after his brother, leaving the angel and the demon alone.

“Is everything okay?” Ruby asked.

Castiel looked at her curiously. “You lied to me…”

“By omission,” Ruby interrupted. Castiel glared at her. “Mostly.” She pursed her lips and pulled her hair back. “I thought if you could figure out what Nate wanted, it would be better than just showing up, all guns blazing, okay? I didn’t want to get into another showdown with a psycho angel. And I knew you’d follow my lead.”

Castiel’s eyes slanted towards her, his head tilted as if listening to the meaning behind her words, rather than the words themselves. She kept herself very still, refusing to back down. She’d had a plan and she’d acted on it and nobody had got hurt. Except her, a tiny voice in the back of her mind shouted, but she quieted it down for now. Laying the groundwork required sacrifices to be made.

“You put the Winchester’s in grave danger.”

Ruby shrugged. “They’re used to it.”

“Be that as it may…this situation could have been avoided…”

“If I’d told you what he was planning he’d have vanished and you’d never have found out about him.” She paused and whispered, almost too quietly for him to hear, “And maybe now you’ll be a little less trusting.”

“I will have to report to my superiors,” he told her. “Your contribution will be noted.” Ruby wasn’t totally sure she was happy about that, but she found herself trusting that Castiel would paint her in the best light possible.

“I did good though, right?” Ruby asked, seeking reassurance.

The angel sighed and Ruby took a few steps forward. She placed her hand on his arm and though he stared down at it he didn’t shake it off, accepting it for the comfort it was meant to be.

“Yes, Ruby, you did good.”


End file.
